U.S. Pat. No. 3,367,943 is directed to a process for preparing oil soluble additives, useful as sludge dispersants, which comprises reacting a C.sub.2 to C.sub.5 alkylene oxide with either (a) an alkylene succinimide derived from an aliphatic polyamine, or (b) the products obtained by reacting an alkenyl succinic anhydride, a C.sub.l to C.sub.30 aliphatic hydrocarbon carboxylic acid and an aliphatic polyamine.
U.S. Pat. No. 3,373,111 is directed to oil-soluble nitrogen-containing compositions prepared by a process which comprises treating an acylated amine with at least 0.2 equivalents of an organic monoepoxide. The acylated amine is prepared by reacting an alkylene amine with from about 0.2 to 2 equivalents of certain acid-producing compounds, including hydrocarbyl-substituted succinic acids wherein the hydrocarbyl substituent has at least about 50 aliphatic carbon atoms. The organic epoxides which are disclosed are unsubstituted or halo-substituted.
U.S. Pat. No. 3,579,450 relates to post-treatment of oil soluble esters of mono- or polycarboxylic acids and polyhydric alcohols with from about 0.05 to 5 equivalents of an organic epoxide per equivalent of alcohol present in the ester. The organic epoxides comprise hydrocarbyl and halo-substituted hydrocarbyl epoxides. U.S. Pat. Nos. 3,859,318; 3,552,179; and 3,381,022 contain a similar disclosure of organic epoxides.
U.S. Pat. No. 3,632,510 is directed to mixed ester-metal salts which, in one embodiment, are obtained by reaction of a hydrocarbyl substituted succinic acid or anhydride with an epoxide to form an acidic ester containing unesterified carboxylic acylating groups, which is then reacted with a basically reacting metal compound to convert the unesterified carboxylic acylating groups to metal carboxylate groups. Epoxides cited as suitable are ethylene oxide, propylene oxide, styrene oxide, 1,2-butylene oxide, 2,3-butylene oxide, epichlorohydrin, cyclohexene oxide, 1,2-octylene oxide, epoxidized soya bean oil, methyl ester of 9,10-epoxy-stearic acid and butadiene epoxide. These esterification reactions are disclosed to involve ring-opening of the selected epoxide as illustrated by the reaction of ethylene oxide with a substituted succinic acid to form hydroxy-terminated esters of the formula: ##STR1## when one mole of the substituted succinic acid is reacted with one or two moles of ethylene oxide, respectively.
U.S. Pat. No. 3,630,904 discloses the pretreatment of a polyalkylene amine with an epoxide to form an intermediate which is then reacted with a hydrocarbyl-substituted succinic acid or anhydride to form a lubricating oil dispersant material. Epoxides disclosed as suitable include glycidol, ethyl ether of glycidol, amyl ether of glycidol and phenyl glycidol. However, such prereaction of the polyalkylene amine and epoxides results in phase-separation, which makes subsequent reactions to form an acceptable oil-soluble dispersant difficult. In an alternate process, the patent discloses the reaction of the hydrocarbyl-substituted succinic acid or anhydride with a polyamine, followed by reaction of the product with at least one of the above epoxides.
U.S. Pat. No. 4,386,939 relates to compositions useful as detergents and dispersants in lubricants and fuels which are prepared by reacting aminophenols and 3- or 4-membered ring heterocyclic compounds. Useful heterocyclic compounds are disclosed to include epoxides, episulfides, aziridines, oxetanes, thietanes and azetidines. Disclosed as epoxides are ethylene oxide, propylene oxide, the butene oxides, epichlorohydrin, glycidol and styrene oxide.
U.S. Pat. No. 4,492,642 is directed to additives, useful in lubricants and liquid fuels (as friction reducers, antioxidants or antiwear corrosivity reducers), which are made by reacting a borating agent with an aminated hydrocarbyl epoxide prepared by reacting a hydrocarbyl epoxide with ammonia or an ammonium compound (e.g., ammonium hydroxide).
U.S. Pat. No. 4,579,674 is directed to hydrocarbyl succinimides of a secondary hydroxyl-substituted polyamine prepared by first reacting a diamine or polyamine with a glycidyl halide, such as epichlorohydrin, to form an intermediate compound characterized by having one or more secondary hydroxyl groups, followed by reaction by this intermediate compound with a hydrocarbyl-substituted succinic anhydride. The patent requires that the amine chain in the resultant molecule be characterized by having a structural unit with a secondary hydroxyl group. The materials are disclosed to be useful as dispersants for lubricating oil compositions.
U.S. Pat. Nos. 4,617,137 and 4,631,070 is directed to additives useful as dispersants in lubricating oils and the like which comprise alkenyl or aryl succinimides which have been modified by treatment with glycidol. The alkenyl or alkyl succinimides are first prepared by a reaction of an alkenyl-substituted succinic anhydride with a selected polyamine, and the resulting succinimide is then contacted for reaction with glycidol, at a glycidol to basic amine nitrogen mole ratio of from about 0.2 to 1 to about 10 to 1.
Co-pending application Ser. No. 122,832, filed Nov. 19, 1987, is directed to chain-extended dispersants, prepared, for example, by contacting a long chain hydrocarbyl substituted succinimide, derived from polyalkylene polyamines, with a polyepoxide.